NP-MRD: Showing NP-Card for BE-54238A (NP0003196)

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Record Information

Version

1.0

Created at

2020-12-09 00:31:46 UTC

Updated at

2022-11-15 23:06:26 UTC

NP-MRD ID

NP0003196

Secondary Accession Numbers

None

Natural Product Identification

Common Name

BE-54238A

Provided By

NPAtlas

Description

BE-54238A is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. BE-54238A is found in Streptomyces and Streptomyces sp. A54238. It was first documented in 2000 (PMID: 10724004). Based on a literature review very few articles have been published on BE-54238A.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117463D          

 52 56  0  0  0  0            999 V2000
    4.2009   -1.4689   -0.7645 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0154   -0.5664   -0.8242 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2586    0.6731   -0.3128 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2914    1.6047   -0.4384 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6832    2.7025   -1.4343 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9181    3.3911   -0.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4015    4.3246   -1.6712 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5732    3.0354    0.1808 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8920    1.0846   -0.7688 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7174   -0.2302   -0.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7537   -3.2242    0.3643 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5068   -2.7409    0.9518 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242117463D          

 52 56  0  0  0  0            999 V2000
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    3.0154   -0.5664   -0.8242 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -3.8499    3.1253   -0.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3978    0.5559   -1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5335    1.7996    1.9919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5011    1.5399    0.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1580   -0.3463    2.5080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5814   -0.7859    0.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0518   -3.5008    2.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3197   -5.2143    2.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
 16 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 11  2  1  0  0  0  0
 28 14  1  0  0  0  0
 19 10  1  0  0  0  0
 19 15  2  0  0  0  0
 25 17  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  2 33  1  6  0  0  0
  4 34  1  1  0  0  0
  5 35  1  0  0  0  0
  5 36  1  0  0  0  0
  8 37  1  0  0  0  0
  9 38  1  0  0  0  0
  9 39  1  0  0  0  0
 13 40  1  0  0  0  0
 20 41  1  1  0  0  0
 21 42  1  6  0  0  0
 22 43  1  0  0  0  0
 22 44  1  0  0  0  0
 22 45  1  0  0  0  0
 23 46  1  0  0  0  0
 24 47  1  0  0  0  0
 24 48  1  0  0  0  0
 25 49  1  0  0  0  0
 25 50  1  0  0  0  0
 26 51  1  0  0  0  0
 27 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003196

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])[C@]1([H])O[C@]([H])(C2=C(C3=C4C(C([H])=C([H])C(=O)C4=C2O[H])=C2N3[C@]([H])(C([H])([H])C2([H])[H])[C@@]([H])(O[H])C([H])([H])[H])C1([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H23NO6/c1-9(24)14-4-5-15-12-3-6-16(25)20-19(12)21(23(14)15)13-7-11(8-17(26)27)29-10(2)18(13)22(20)28/h3,6,9-11,14,24,28H,4-5,7-8H2,1-2H3,(H,26,27)/t9-,10-,11+,14+/m0/s1

> <INCHI_KEY>
AWMWNWIBOOYESP-UHFFFAOYSA-N

> <FORMULA>
C22H23NO6

> <MOLECULAR_WEIGHT>
397.427

> <EXACT_MASS>
397.152537465

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
42.006980271605514

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(3R,14S,16R)-12-hydroxy-3-[(1S)-1-hydroxyethyl]-14-methyl-10-oxo-15-oxa-2-azapentacyclo[9.7.1.0^{2,6}.0^{7,19}.0^{13,18}]nonadeca-1(19),6,8,11,13(18)-pentaen-16-yl]acetic acid

> <ALOGPS_LOGP>
1.96

> <JCHEM_LOGP>
2.7277465296666668

> <ALOGPS_LOGS>
-3.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.081273249566278

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8744341777245217

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8742712608678085

> <JCHEM_POLAR_SURFACE_AREA>
108.99000000000001

> <JCHEM_REFRACTIVITY>
106.85619999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.95e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(3R,14S,16R)-12-hydroxy-3-[(1S)-1-hydroxyethyl]-14-methyl-10-oxo-15-oxa-2-azapentacyclo[9.7.1.0^{2,6}.0^{7,19}.0^{13,18}]nonadeca-1(19),6,8,11,13(18)-pentaen-16-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
    4.2009   -1.4689   -0.7645 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0154   -0.5664   -0.8242 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2586    0.6731   -0.3128 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2914    1.6047   -0.4384 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6832    2.7025   -1.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9181    3.3911   -0.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4015    4.3246   -1.6712 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5732    3.0354    0.1808 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8920    1.0846   -0.7688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7174   -0.2302   -0.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8128   -1.1074   -0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7243   -2.3712    0.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7537   -3.2242    0.3643 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5068   -2.7409    0.9518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5455   -1.8605    0.9580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7855   -2.0504    1.4674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4929   -0.8764    1.2308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6772    0.0058    0.5848 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4699   -0.6021    0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3460    1.2298    0.3174 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7115    1.3463   -1.1670 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4146    2.6294   -1.4588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5207    0.2506   -1.5219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6323    1.1480    1.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8219   -0.2994    1.4487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0636   -3.3503    2.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0909   -4.2574    2.1294 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2534   -4.0289    1.5676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1516   -4.8739    1.6009 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5371   -1.7188    0.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0486   -0.9370   -1.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0059   -2.3612   -1.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7604   -0.4345   -1.9134 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2051    2.1429    0.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8192    3.4026   -1.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8221    2.2913   -2.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0796    3.0806    1.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8749    0.9108   -1.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2199    1.8760   -0.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9885   -4.1081    0.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7848    2.1539    0.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8053    1.2682   -1.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    3.3360   -1.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2689    2.4068   -2.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8499    3.1253   -0.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3978    0.5559   -1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5335    1.7996    1.9919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5011    1.5399    0.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1580   -0.3463    2.5080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5814   -0.7859    0.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0518   -3.5008    2.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3197   -5.2143    2.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 20 24  1  0
 24 25  1  0
 16 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 11  2  1  0
 28 14  1  0
 19 10  1  0
 19 15  2  0
 25 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  6
  4 34  1  1
  5 35  1  0
  5 36  1  0
  8 37  1  0
  9 38  1  0
  9 39  1  0
 13 40  1  0
 20 41  1  1
 21 42  1  6
 22 43  1  0
 22 44  1  0
 22 45  1  0
 23 46  1  0
 24 47  1  0
 24 48  1  0
 25 49  1  0
 25 50  1  0
 26 51  1  0
 27 52  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       4.201  -1.469  -0.765  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.015  -0.566  -0.824  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.259   0.673  -0.313  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.291   1.605  -0.438  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.683   2.703  -1.434  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.918   3.391  -0.988  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.402   4.325  -1.671  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.573   3.035   0.181  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.892   1.085  -0.769  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.717  -0.230  -0.155  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.813  -1.107  -0.178  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.724  -2.371   0.374  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.754  -3.224   0.364  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.507  -2.741   0.952  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.546  -1.861   0.958  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.786  -2.050   1.467  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.493  -0.876   1.231  0.00  0.00           C+0
HETATM   18  N   UNK     0      -1.677   0.006   0.585  0.00  0.00           N+0
HETATM   19  C   UNK     0      -0.470  -0.602   0.414  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.346   1.230   0.317  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.712   1.346  -1.167  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.415   2.629  -1.459  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.521   0.251  -1.522  0.00  0.00           O+0
HETATM   24  C   UNK     0      -3.632   1.148   1.099  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.822  -0.299   1.449  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.064  -3.350   2.097  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.091  -4.257   2.129  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.253  -4.029   1.568  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.152  -4.874   1.601  0.00  0.00           O+0
HETATM   30  H   UNK     0       4.537  -1.719   0.244  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.049  -0.937  -1.261  0.00  0.00           H+0
HETATM   32  H   UNK     0       4.006  -2.361  -1.410  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.760  -0.435  -1.913  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.205   2.143   0.553  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.819   3.403  -1.450  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.822   2.291  -2.442  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.080   3.081   1.048  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.875   0.911  -1.888  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.220   1.876  -0.471  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.989  -4.108   0.646  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.785   2.154   0.567  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.805   1.268  -1.774  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.691   3.336  -1.938  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.269   2.407  -2.143  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.850   3.125  -0.572  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.398   0.556  -1.833  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.534   1.800   1.992  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.501   1.540   0.535  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.158  -0.346   2.508  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.581  -0.786   0.797  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.052  -3.501   2.502  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.320  -5.214   2.601  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    1    3   11   33                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    9   34                                             
CONECT    5    4    6   35   36                                             
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6   37                                                       
CONECT    9    4   10   38   39                                             
CONECT   10    9   11   19                                                  
CONECT   11   10   12    2                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12   40                                                       
CONECT   14   12   15   28                                                  
CONECT   15   14   16   19                                                  
CONECT   16   15   17   26                                                  
CONECT   17   16   18   25                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   10   15                                                  
CONECT   20   18   21   24   41                                             
CONECT   21   20   22   23   42                                             
CONECT   22   21   43   44   45                                             
CONECT   23   21   46                                                       
CONECT   24   20   25   47   48                                             
CONECT   25   24   17   49   50                                             
CONECT   26   16   27   51                                                  
CONECT   27   26   28   52                                                  
CONECT   28   27   29   14                                                  
CONECT   29   28                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    2                                                            
CONECT   34    4                                                            
CONECT   35    5                                                            
CONECT   36    5                                                            
CONECT   37    8                                                            
CONECT   38    9                                                            
CONECT   39    9                                                            
CONECT   40   13                                                            
CONECT   41   20                                                            
CONECT   42   21                                                            
CONECT   43   22                                                            
CONECT   44   22                                                            
CONECT   45   22                                                            
CONECT   46   23                                                            
CONECT   47   24                                                            
CONECT   48   24                                                            
CONECT   49   25                                                            
CONECT   50   25                                                            
CONECT   51   26                                                            
CONECT   52   27                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  112    0
END

RDKit          3D

52 56  0  0  0  0  0  0  0  0999 V2000
    4.2009   -1.4689   -0.7645 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0154   -0.5664   -0.8242 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2586    0.6731   -0.3128 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2914    1.6047   -0.4384 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6832    2.7025   -1.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9181    3.3911   -0.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4015    4.3246   -1.6712 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5732    3.0354    0.1808 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8920    1.0846   -0.7688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7174   -0.2302   -0.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8128   -1.1074   -0.1777 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7243   -2.3712    0.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7537   -3.2242    0.3643 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5068   -2.7409    0.9518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5455   -1.8605    0.9580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7855   -2.0504    1.4674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4929   -0.8764    1.2308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6772    0.0058    0.5848 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4699   -0.6021    0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3460    1.2298    0.3174 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7115    1.3463   -1.1670 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4146    2.6294   -1.4588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5207    0.2506   -1.5219 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6323    1.1480    1.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8219   -0.2994    1.4487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0636   -3.3503    2.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0909   -4.2574    2.1294 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2534   -4.0289    1.5676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1516   -4.8739    1.6009 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5371   -1.7188    0.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0486   -0.9370   -1.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0059   -2.3612   -1.4103 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7604   -0.4345   -1.9134 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2051    2.1429    0.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8192    3.4026   -1.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8221    2.2913   -2.4415 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0796    3.0806    1.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8749    0.9108   -1.8883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2199    1.8760   -0.4714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9885   -4.1081    0.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7848    2.1539    0.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8053    1.2682   -1.7740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    3.3360   -1.9376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2689    2.4068   -2.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8499    3.1253   -0.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3978    0.5559   -1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5335    1.7996    1.9919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5011    1.5399    0.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1580   -0.3463    2.5080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5814   -0.7859    0.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0518   -3.5008    2.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3197   -5.2143    2.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  4  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 20 24  1  0
 24 25  1  0
 16 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 11  2  1  0
 28 14  1  0
 19 10  1  0
 19 15  2  0
 25 17  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  6
  4 34  1  1
  5 35  1  0
  5 36  1  0
  8 37  1  0
  9 38  1  0
  9 39  1  0
 13 40  1  0
 20 41  1  1
 21 42  1  6
 22 43  1  0
 22 44  1  0
 22 45  1  0
 23 46  1  0
 24 47  1  0
 24 48  1  0
 25 49  1  0
 25 50  1  0
 26 51  1  0
 27 52  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
[7-Hydroxy-1-(1-hydroxyethyl)-8-methyl-6-oxo-1,2,3,8,10,11-hexahydro-6H-benzo[CD]pyrano[3,4-g]pyrrolo[1,2-a]indol-10-yl]acetate	Generator

Chemical Formula

C₂₂H₂₃NO₆

Average Mass

397.4270 Da

Monoisotopic Mass

397.15254 Da

IUPAC Name

2-[(3R,14S,16R)-12-hydroxy-3-[(1S)-1-hydroxyethyl]-14-methyl-10-oxo-15-oxa-2-azapentacyclo[9.7.1.0^{2,6}.0^{7,19}.0^{13,18}]nonadeca-1(19),6,8,11,13(18)-pentaen-16-yl]acetic acid

Traditional Name

[(3R,14S,16R)-12-hydroxy-3-[(1S)-1-hydroxyethyl]-14-methyl-10-oxo-15-oxa-2-azapentacyclo[9.7.1.0^{2,6}.0^{7,19}.0^{13,18}]nonadeca-1(19),6,8,11,13(18)-pentaen-16-yl]acetic acid

CAS Registry Number

Not Available

SMILES

CC(O)C1CCC2=C3C=CC(=O)C4=C3C(N12)=C1CC(CC(O)=O)OC(C)C1=C4O

InChI Identifier

InChI=1S/C22H23NO6/c1-9(24)14-4-5-15-12-3-6-16(25)20-19(12)21(23(14)15)13-7-11(8-17(26)27)29-10(2)18(13)22(20)28/h3,6,9-11,14,24,28H,4-5,7-8H2,1-2H3,(H,26,27)

InChI Key

AWMWNWIBOOYESP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces	NPAtlas	10724004
Streptomyces sp. A54238	Bacteria	KNApSAcK

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as naphthopyranones. These are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Naphthopyranone
Hydroxyindole
2-benzopyran
Naphthalene
Isoindolone
Isochromane
Benzopyran
Isoindole or derivatives
Indole or derivatives
Indole
Aryl ketone
Pyrrolizine
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Pyrrole
Secondary alcohol
Ketone
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.96	ALOGPS
logP	2.73	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.87	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	108.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	106.86 m³·mol⁻¹	ChemAxon
Polarizability	42.01 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA013050

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8106309

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

65475

Good Scents ID

Not Available

References

General References

Tsukamoto M, Nakajima S, Murooka K, Hirayama M, Hirano K, Yoshida S, Kojiri K, Suda H: New cytotoxic agents, BE-54238A and B, produced by a streptomycete. J Antibiot (Tokyo). 2000 Jan;53(1):26-32. doi: 10.7164/antibiotics.53.26. [PubMed:10724004 ]

Showing NP-Card for BE-54238A (NP0003196)

MOL for NP0003196 (BE-54238A)

3D MOL for NP0003196 (BE-54238A)

3D SDF for NP0003196 (BE-54238A)

3D-SDF for NP0003196 (BE-54238A)

PDB for NP0003196 (BE-54238A)

3D PDB for NP0003196 (BE-54238A)

SMILES for NP0003196 (BE-54238A)

INCHI for NP0003196 (BE-54238A)

Structure for NP0003196 (BE-54238A)

3D Structure for NP0003196 (BE-54238A)